Difunctionalization of Cyclopropyl Amines with N-lodosuccinirnide (NIS) or in Situ Formed Cyanogen Iodide (ICN)
by Wang, Qile; Zheng, Nan
We report herein a 1,3-difunctionalization of c-yclopropylamines thaf serve as 'a A- nucleophile in a two electron (2e) 5,2-like ring opening pathway. N-Iodosuccinimide (NIS) or in situ generated cyanogen iodide (ICN) is employed as electrophilic iodinating reagents in conjunction with TMSCN or succinimide to furnish multiple pairs of functional groups disposed in a 1,3 -manner. This 2e ring opening manifold overcomes the constraint of our previously reported le protocol as demonstrated by successful activation of monocyclic tertiary cyclopropylamines.
- Journal
- Organic Letters
- Volume
- 21
- Issue
- 24
- Year
- 2019
- Start Page
- 9999-10002
- URL
- https://dx.doi.org/10.1021/acs.orglett.9b03922
- ISBN/ISSN
- 1523-7052; 1523-7060
- DOI
- 10.1021/acs.orglett.9b03922